(E)-2-[(2-Hydr-oxy-5-nitro-phen-yl)iminiometh-yl]-4-nitro-phenolate.
(E)-2-[(2-Hydr-oxy-5-nitro-phen-yl)iminiometh-yl]-4-nitro-phenolate.
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(E)-2-[(2-羟基-5-硝基-苯基)亚氨基甲基]-4-硝基-苯酚盐。
DOI：
10.1107/s1600536809000543
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发表时间：
2009
期刊：
影响因子：
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通讯作者：
Jasinski,JerryP
中科院分区：
文献类型：
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作者：
Hijji,YousefM;Barare,Belygona;Butcher,RayJ;Jasinski,JerryP
标题化合物C_（13）H_9 N_3 O_6是由2-羟基-5-硝基苯亚氨基和4-硝基酚基与亚甲基C原子键合而成，两个平面六元环几乎在分子平面内[二面角= 1.3（4）°]。 每一个硝基氧原子都轻微地扭曲在分子平面之外。胺基与附近的两个O原子形成分子内氢键，每个O原子都部分占据连接的H原子[0.36（3）和0.64（3）]。 在整个分子中存在扩展的π-离域，在分子的该区域中产生两性离子效应。缩短的酚盐C-O键[1.2749（19）°]与稍长的酚C-O键[1.3316（19）°]一致，为这种效应提供了证据。 晶体堆积受到所描绘的酚盐和羟基O原子与分子的π-离域区域内的它们各自的H原子之间的广泛的强分子间O-H-O氢键的影响。结果，分子以交替的倒置图案沿晶胞的[110]平面对角地沿着连接成无限聚合物链。MOPAC AM 1计算为这些观察提供了支持。
The title molecule, C13H9N3O6, consists of a 2-hydroxy-5-nitrophenyliminio group and a 4-nitrophenolate group bonded to a methylene C atom with both of the planar six-membered rings nearly in the plane of the molecule [dihedral angle = 1.3 (4)°]. Each of the nitro O atoms is twisted slightly out of the plane of the molecule. The amine group forms an intramolecular hydrogen bond with both nearby O atoms, each of which has partial occupancy of attached H atoms [0.36 (3) and 0.64 (3)]. An extended π-delocalization throughout the entire molecule exists producing a zwitterionic effect in this region of the molecule. The shortened phenolate C—O bond [1.2749 (19)°], in concert with the slightly longer phenol C—O bond [1.3316 (19) Å], provides evidence for this effect. The crystal packing is influenced by extensive strong intermolecular O—H⋯O hydrogen bonding between the depicted phenolate and hydroxy O atoms and their respective H atoms within the π-delocalized region of the molecule. As a result, molecules are linked into an infinite polymeric chain diagonally along the [110] plane of the unit cell in an alternate inverted pattern. A MOPAC AM1 calculation provides support for these observations.